In sociology, aesthetics have become an important lens for exploring the sensory dimensions of political and economic processes, with research on urban aesthetics contributing significantly to this field. However, much of this work focuses on how aesthetic forms serve the interests of political and economic elites, portraying aesthetic value as a direct product of political ideologies. While these approaches have shown that urban aesthetics are shaped by power struggles, they pay limited theoretical attention to less straightforward aspects of aesthetic politics—such as cases where clashing values, imperatives, and commitments meet. This gap is particularly pronounced in places shaped by violent histories, where the value of urban beauty might be inevitably entangled with loss, ambivalence, and co-existence with unwanted materialities. This article proposes an approach that foregrounds the dilemmas and compromises inherent in urban aesthetic politics, focusing on the varied practices through which people negotiate how to care for urban aesthetic value over time. I develop this approach through a case study of Klaipėda, Lithuania—a city shaped by layered aesthetic transformations, from state annexation to socialist modernisation to post-Soviet nation-building and Europeanisation. Using mixed-methods research, the article highlights differences in how people articulate what counts as good and bad aesthetics and which forms of material care—or neglect—are “appropriate” to sustain the city’s desirable aesthetic appeal. In doing so, the article reveals complex gradations of value underlying seemingly coherent aesthetic ideals of Europeanness.